2-(1H-Benzotriazol-1-yl)-1-(3-methyl­benzo­yl)ethyl benzoate

Wu-Lan Zeng; Lian-Cai Du; Lei Zhang; Fang-Fang Jian

doi:10.1107/S1600536809026853

. 2009 Jul 18;65(Pt 8):o1882. doi: 10.1107/S1600536809026853

2-(1H-Benzotriazol-1-yl)-1-(3-methylbenzoyl)ethyl benzoate

Wu-Lan Zeng ^a, Lian-Cai Du ^b, Lei Zhang ^b, Fang-Fang Jian ^b,^*

PMCID: PMC2977413 PMID: 21583575

Abstract

In the title molecule, C₂₃H₁₉N₃O₃, the dihedral angles between the mean plane of the benzotriazole ring system and the benzene and phenyl rings are 9.67 (9) and 86.08 (10)°, respectively. The dihedral angle between the benzene and phenyl rings is 85.89 (11)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link molecules into chains along [010].

Related literature

For the pharmacological activities of 1H-benzotriazoles and their derivatives, see: Chen & Wu (2005 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₃H₁₉N₃O₃
M _r = 385.41
Monoclinic,
a = 10.1095 (5) Å
b = 9.3849 (4) Å
c = 20.7091 (10) Å
β = 99.061 (4)°
V = 1940.29 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.10 × 0.10 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.974, T _max = 0.991
16102 measured reflections
3301 independent reflections
2071 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.110
S = 1.00
3301 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026853/lh2841sup1.cif

e-65-o1882-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026853/lh2841Isup2.hkl

e-65-o1882-Isup2.hkl^{(161.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O2ⁱ	0.97	2.42	3.062 (2)	123
C11—H11A⋯O1ⁱⁱ	0.93	2.60	3.375 (2)	141

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

1H-Benzotriazoles and their derivatives are an important class of compounds because they exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu., 2005). Herein, we present the crystal structure of the title compound (I). In (I) (Fig. 1) all bond lengths (Allen et al., 1987) and angles within normal ranges. The benzotriazole ring system is essentially planar. The dihedral angles between the mean plane of the benzotriazole ring system and rings C10—C15 and C18—C23 are 9.67 (9) and 86.08 (10)°, respectively. The dihedral angle between rings C10—C15 and C19—C23 is 85.89 (11)°. In the crystal structure weak intermolecular C—H···O hydrogen bonds link molecules into chains along [010] (see Fig. 2).

Experimental

Bromine (3.2 g,0.02 mol) was added dropwise to a solution of 3-(1H-benzo[d][1,2,3]triazol-1-yl)-1-m-tolylpropan-1-one (5.30 g,0.02 mol) and sodium acetate (1.6 g,0.02 mol) in acetic acid (50 ml). The reaction proceeded for 8 h. Water (50 ml) and chloroform (20 ml) were then added. The organic layer was washed successively with saturated sodium bicarbonate solution and brine, dried over anhydrou magnesium sulfate and the chloroform solution filtered. It was cooled with ice-water, and then an acetone solution (10 ml) of benzoic acid (2.24 g,0.02 mol) and triethylamine (2.8 ml) was added. The mixture was stirred with ice-water for about 6 h. The solution was then filtered and concentrated. Single crystals were obtained by slow evaporation of an acetone-ethylacetate (1:1 v/v) solution of (I) at room temperature over a period of one week.